Acetic Anhydride → HCID 13457334, compound

HRID 463285Notes

Reaction equation

HRID 463285 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=2)[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:27])[CH3:26])[CH:19]=2)[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 13457329HCID 13457329, compound

Product 1

HCID 13457334HCID 13457334, compound

Procedure

The resulting ethereal solution from Example 4 containing 1-[4-(4-chlorophenyl)-2-(3-aminophenylthio)-n-butyl]imidazole was treated at room temperature with stirring with acetic anhydride (1.5 m.). After stirring overnight, the mixture was evaporated to dryness in vacuo and the residue chromatographed on silica gel eluting with methylene chloride followed by 2.2% water in ethyl acetate. The resulting pure product, 1-[4-(4-chlorophenyl)-2-(3-acetylaminophenylthio)-n-butyl]imidazole, obtained as a gum, was dissolved in a small volume of methanol and treated with excess ethereal hydrogen chloride. The solution was filtered, evaporated almost to dryness and evacuated in a warm water bath to give 1-[4-(4-chlorophenyl)-2-(3-acetylaminophenylthio)-n-butyl]imidazole hydrochloride 1.79 g as a brittle foam, dec 87°-92° C.

Workup

  1. customthe mixture was evaporated to dryness in vacuo
  2. customthe residue chromatographed on silica gel eluting with methylene chloride

Sources & evidence

ORD record
ord-0e040f69a56e446591fa375894ef2b52
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

Loading…